Biotransformations versus chemical modifications: new cytotoxic analogs of marine sesquiterpene ilimaquinone
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Petek, Sylvain
Evanno, Laurent
Beniddir, Mehdi A
Debitus, Cecile
Buisson, Didier
Poupon, Erwan
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Abstract
Highly biologically active marine sesquiterpene ilimaquinone was selected for chemical modifications. Its biotransformation was investigated using a combinatorial approach as an original way to screen different strains of microorganisms. Mucor circinelloides ATCC 8541 was able to structurally modify ilimaquinone into three different compounds. A stereospecific epoxidation was observed and compared to chemical epoxidation. A hydroxylation of the decalin ring was also observed as well as an unexpected substitution on the quinone ring by ethanolamine. Compounds were evaluated against several cell lines.
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Tetrahedron Letters
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57
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Medicinal and biomolecular chemistry
Medicinal and biomolecular chemistry not elsewhere classified
Organic chemistry